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LA-Aziridine
Pharmaceutical compound From Wikipedia, the free encyclopedia
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LA-Aziridine, also known as N-(2,3-dimethylaziridin-1-yl)lysergamide or as lysergic acid-(2,3-dimethylaziridinyl)amide, is a chemical compound of the lysergamide family related to lysergic acid diethylamide (LSD).[1][2][3][4] It is an analogue of LSD in which the N,N-diethyl groups have been fused together to form an N-(2,3-dimethylaziridine) ring moiety.[1][3][4] The compound has two additional chiral centers in the aziridine region and thus has three diastereomeric forms: (R,R)-trans, (S,S)-trans, and cis.[4] LA-Aziridine is closely related to lysergic acid 2,4-dimethylazetidide (LA-Az, LSZ, or LA-Azetidide).[2]
The laboratory of David E. Nichols and colleagues synthesized LA-Aziridine in the 1980s while studying the influence of stereoselectivity on lysergamide activity.[1][2][4] However, LA-Aziridine proved to be chemically unstable such that in-vivo usefulness was precluded, and they abandoned their efforts with the compound.[1][2][4] Instead, the group studied LA-3Cl-SB, another analogue of LSD in which the diethylamide moiety was replaced with a 2-chloro-1-methylpropylamide moiety and that had four possible stereoisomers.[1][4] These stereoisomers successfully substituted for LSD in rodent drug discrimination tests with varying potencies.[1][4] In addition, Nichols and colleagues subsequently turned their attention to LSZ, which proved active and did not have the stability problems of LA-Aziridine.[2][5]
Other analogues besides LA-Aziridine and LSZ have also been studied, for instance the N-(2,5-dimethylpyrrolidide) (a derivative of LA-Pyr) and the N-(2,6-dimethylpiperidide) (a derivative of LA-Pip) analogues.[6][7]
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